Sodium triacetoxyborohydride → (+/-)-(3-{[1-(3-benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-cyclohexyl-amino}-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 1795986Notes

Reaction equation

HRID 1795986 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:18]([NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1[C:40]2[CH:39]([CH2:41][O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH:47]=O)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:37]1[C:38]2[CH:39]([CH2:41][O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH2:47][N:21]([CH:18]([C:9]3[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:13](=[O:14])[C:12]4=[CH:15][CH:16]=[CH:17][N:11]4[N:10]=3)[CH2:19][CH3:20])[CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:40]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]=2[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11277844Carbamic acid, (3-oxopropyl)-, 9H-fluoren-9-ylmethyl esterHCID 221800673-Benzyl-2-(1-cyclohexylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Product 1

HCID 69591832(+/-)-(3-{[1-(3-benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-cyclohexyl-amino}-propyl)-carbamic acid 9H-fluoren-9-ylmethyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-benzyl-2-(1-cyclohexylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 28, 150 mg, 0.41 mmol), (3-oxo-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (Org. Lett. 2002, 4, 3001–3003, 184 mg, 0.62 mmol), acetic acetic (1.5 eq), 4 Å molecular sieves (100 mg), and 1,2-dichloroethane (10 mL) was stirred at room temperature for 30 min, then treated with sodium triacetoxyborohydride (130 mg, 0.62 mmol). After 3 h, the mixture was filtered and the filtrate washed with saturated sodium bicarbonate and water, dried (MgSO4), and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes to give the title compound as a white solid (115 mg, 44%): MS (ESI+) 644.44 (M++H).

Workup

  1. waitAfter 3 h
  2. filtrationthe mixture was filtered
  3. washthe filtrate washed with saturated sodium bicarbonate and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-131efe79b1fd48278b7296316573718a
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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